Compound

ABSTRACT

A compound is represented by the following formula (1). In the formula (1), Ar is a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, R a  are independently a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, R b1  to R b4  are independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or the like, R c1  to R c10  are independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or the like, * is a bonding position at which one of R c1  to R c10  is bonded to either nitrogen atom, x is an integer from 0 to 3, y is an integer from 0 to 4, and z are independently an integer from 0 to 5.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of U.S. patent applicationSer. No. 14/908,929, filed Jan. 29, 2016, which is a U.S. National StageEntry of International Patent Application No. PCT/JP2015/004810, filedSep. 18, 2015, which claims the benefit of priority from Japanese PatentApplication No. 2014-191964, filed Sep. 19, 2014, the entireties ofwhich are all hereby incorporated herein by reference.

TECHNICAL FIELD

The invention relates to a novel compound and an organicelectroluminescence device using the same.

BACKGROUND ART

An organic electroluminescence (EL) device is considered to be apromising inexpensive large full-color display that utilizes solid-stateemission, and has been extensively developed. The organic EL devicenormally includes an emitting layer, and a pair of opposing electrodesthat are disposed on either side of the emitting layer. When an electricfield is applied between the electrodes, electrons are injected from thecathode, and holes are injected from the anode. The electrons and theholes recombine in the emitting layer to produce an excited state, andthe energy is emitted as light when the excited state returns to theground state.

A known organic EL device has problems in that a high driving voltage isrequired, and only low luminance and low luminous (emission) efficiencycan be achieved. It is important to improve the luminous efficiency ofan organic EL device in order to reduce the power consumption of adisplay, and the materials used to produce an organic EL device havebeen gradually improved in recent years (see Patent Documents 1 and 2,for example). However, a further improvement in efficiency has beendesired.

CITATION LIST Patent Literature

Patent Document 1: JP-A-2013-118288

Patent Document 2: JP-A-2011-153201

SUMMARY OF INVENTION

An object of the invention is to provide a compound that makes itpossible to produce an organic EL device that exhibits excellentluminous efficiency.

One aspect of the invention provides the following compound, forexample.

A compound represented by the following formula (1),

wherein Ar is a substituted or unsubstituted aryl group including 6 to30 carbon atoms that form a ring (hereinafter referred to as “ringcarbon atoms”),R^(a) are independently a substituted or unsubstituted alkyl groupincluding 1 to 15 carbon atoms, or a substituted or unsubstitutedcycloalkyl group including 3 to 15 carbon atoms,R^(b1) to R^(b4) are independently a halogen atom, a cyano group, asubstituted or unsubstituted alkyl group including 1 to 15 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 15 carbonatoms, a substituted or unsubstituted alkylsilyl group including 1 to 45carbon atoms, a substituted or unsubstituted arylsilyl group including 6to 50 carbon atoms, a substituted or unsubstituted alkoxy groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted aryloxygroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted alkylthio group including 1 to 15 carbon atoms, asubstituted or unsubstituted arylthio group including 6 to 30 ringcarbon atoms, a substituted or unsubstituted arylamino group including 6to 30 ring carbon atoms, a substituted or unsubstituted aryl groupincluding 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group including 3 to 30 atoms that form a ring (hereinafterreferred to as “ring atoms”), R^(c1) to R^(c10) are independently ahydrogen atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 15 carbonatoms,a substituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms,a substituted or unsubstituted arylsilyl group including 6 to 50 carbonatoms,a substituted or unsubstituted alkoxy group including 1 to 15 carbonatoms,a substituted or unsubstituted aryloxy group including 6 to 30 ringcarbon atoms,a substituted or unsubstituted alkylthio group including 1 to 15 carbonatoms,a substituted or unsubstituted arylthio group including 6 to 30 ringcarbon atoms,a substituted or unsubstituted arylamino group including 6 to 30 ringcarbon atoms, a substituted or unsubstituted aryl group including 6 to30 ring carbon atoms, a substituted or unsubstituted heteroaryl groupincluding 3 to 30 ring atoms, or a single bond that is bonded to eithernitrogen atom,* is a bonding position at which one of R^(c1) to R^(c10) is bonded toeither nitrogen atom,x is an integer from 0 to 3,y is an integer from 0 to 4,z are independently an integer from 0 to 5,a plurality of R^(b1) are either identical or different when x is aninteger equal to or larger than 2, a plurality of R^(b2) are eitheridentical or different when y is an integer equal to or larger than 2,and a plurality of R^(b3) or R^(b4) are either identical or differentwhen z is an integer equal to or larger than 2.

The invention thus provides a compound that makes it possible to producean organic EL device that exhibits excellent luminous efficiency.

DESCRIPTION OF EMBODIMENTS

The compound according to one aspect of the invention is represented bythe following formula (1).

Ar in the formula (1) is a substituted or unsubstituted aryl groupincluding 6 to 30 ring carbon atoms.

R^(a) are independently a substituted or unsubstituted alkyl groupincluding 1 to 15 carbon atoms, or a substituted or unsubstitutedcycloalkyl group including 3 to 15 carbon atoms.

R^(b1) to R^(b4) are independently a halogen atom, a cyano group, asubstituted or unsubstituted alkyl group including 1 to 15 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 15 carbonatoms, a substituted or unsubstituted alkylsilyl group including 1 to 45carbon atoms, a substituted or unsubstituted arylsilyl group including 6to 50 carbon atoms, a substituted or unsubstituted alkoxy groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted aryloxygroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted alkylthio group including 1 to 15 carbon atoms, asubstituted or unsubstituted arylthio group including 6 to 30 ringcarbon atoms, a substituted or unsubstituted arylamino group including 6to 30 ring carbon atoms, a substituted or unsubstituted aryl groupincluding 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group including 3 to 30 ring atoms.

R^(c1) to R^(c10) are independently a hydrogen atom, a halogen atom, acyano group, a substituted or unsubstituted alkyl group including 1 to15 carbon atoms, a substituted or unsubstituted cycloalkyl groupincluding 3 to 15 carbon atoms, a substituted or unsubstitutedalkylsilyl group including 1 to 45 carbon atoms, a substituted orunsubstituted arylsilyl group including 6 to 50 carbon atoms, asubstituted or unsubstituted alkoxy group including 1 to 15 carbonatoms, a substituted or unsubstituted aryloxy group including 6 to 30ring carbon atoms, a substituted or unsubstituted alkylthio groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted arylthiogroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, a substituted or unsubstituted heteroaryl group including 3 to 30ring atoms, or a single bond that is bonded to either nitrogen atom.

* is a bonding position at which any of R^(c1) to R^(c10) is bonded toeither nitrogen atom.

x is an integer from 0 to 3, y is an integer from 0 to 4, and z areindependently an integer from 0 to 5. A plurality of R^(b1) are eitheridentical or different when x is an integer equal to or larger than 2, aplurality of R^(b2) are either identical or different when y is aninteger equal to or larger than 2, and a plurality of R^(b3) or R^(b4)are either identical or different when z is an integer equal to orlarger than 2.

The compound according to one aspect of the invention exhibits excellentluminous efficiency when used for an organic EL device due to the abovespecific structure.

The compound is preferably represented by the following formula (2).

Ar, R^(a), R^(b1) to R^(b4), R^(c1) to R^(c10), x, z, and * in theformula (2) are the same as defined for the formula (1).

It is preferable that R^(c1) to R^(c10) be independently a group otherthan an arylamino group. Specifically, it is preferable that R^(c1) toR^(c10) be independently a hydrogen atom, a halogen atom, a cyano group,a substituted or unsubstituted alkyl group including 1 to 15 carbonatoms, a substituted or unsubstituted cycloalkyl group including 3 to 15carbon atoms, a substituted or unsubstituted alkylsilyl group including1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl groupincluding 6 to 50 carbon atoms, a substituted or unsubstituted alkoxygroup including 1 to 15 carbon atoms, a substituted or unsubstitutedaryloxy group including 6 to 30 ring carbon atoms, a substituted orunsubstituted alkylthio group including 1 to 15 carbon atoms, asubstituted or unsubstituted arylthio group including 6 to 30 ringcarbon atoms, a substituted or unsubstituted aryl group including 6 to30 ring carbon atoms, a substituted or unsubstituted heteroaryl groupincluding 3 to 30 ring atoms, or a single bond that is bonded to eithernitrogen atom.

In this case, the compound is an arylamino group-disubstitution product.

The compound is preferably represented by the following formula (3), andmore preferably represented by the following formula (4).

Ar, R^(a), R^(b1) to R^(b4), R^(c2) to R^(c10), x, z, and * in theformula (3) are the same as defined for the formula (1).

Ar, R^(a), R^(b1) to R^(b4), x, and z in the formula (4) are the same asdefined for the formula (1).

R^(c2) to R^(c5) and R^(c7) to R^(c10) are independently a hydrogenatom, a halogen atom, a cyano group, a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, a substituted or unsubstituted alkoxy group including 1 to15 carbon atoms, a substituted or unsubstituted aryloxy group including6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 15 carbon atoms, a substituted or unsubstitutedarylthio group including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms.

When the compound is represented by the formula (4), the compound ismore preferably represented by the following formula (4-1).

Ar, R^(a), R^(b1) to R^(b4), R^(c3), R^(c8), x, and z in the formula(4-1) are the same as defined for the formula (4).

It is preferable that R^(c) and R be independently a hydrogen atom, analkyl group including 1 to 6 carbon atoms, or a cycloalkyl groupincluding 1 to 6 carbon atoms.

The compound is preferably represented by the following formula (5).

Ar, R^(a), R^(b1) to R^(b4), x, and z in the formula (5) are the same asdefined for the formula (1). R^(c2) and R^(c4) to R^(c10) areindependently a hydrogen atom, a halogen atom, a cyano group, asubstituted or unsubstituted alkyl group including 1 to 15 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 15 carbonatoms, a substituted or unsubstituted alkylsilyl group including 1 to 45carbon atoms, a substituted or unsubstituted arylsilyl group including 6to 50 carbon atoms, a substituted or unsubstituted alkoxy groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted aryloxygroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted alkylthio group including 1 to 15 carbon atoms, asubstituted or unsubstituted arylthio group including 6 to 30 ringcarbon atoms, a substituted or unsubstituted arylamino group including 6to 30 ring carbon atoms, a substituted or unsubstituted aryl groupincluding 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group including 3 to 30 ring atoms.

When the compound is represented by the formula (5), the compound ismore preferably represented by the following formula (5-1).

Ar, R^(a), R^(b1) to R^(b4), R^(c7), x, and z in the formula (5-1) arethe same as defined for the formula (5).

It is preferable that R^(c7) be a substituted or unsubstituted alkylgroup including 1 to 15 carbon atoms, or a substituted or unsubstitutedcycloalkyl group including 3 to 15 carbon atoms.

It is preferable that the benzene ring-containing group in the formula(1) to which R^(b1) is bonded, and the benzene ring-containing group inthe formula (1) to which R^(b2) is bonded, have a structure in which thebenzene ring-containing group is not substituted with a substituent(i.e., a hydrogen atom is bonded) at the para position with respect tothe bonding position at which the N atom is bonded. Specifically, it ispreferable that the benzene ring-containing group to which R^(b1) isbonded have a structure in which R^(b1) and Ar are not bonded at thepara position with respect to the bonding position at which the N atomis bonded, and the benzene ring-containing group to which R^(b2) isbonded have a structure in which R^(b2) is not bonded at the paraposition with respect to the bonding position at which the N atom isbonded. Likewise, it is preferable that the benzene ring-containinggroup in the formula (2) and the like to which R^(b1) is bonded have astructure in which R^(b1) and Ar are not bonded at the para positionwith respect to the bonding position at which the N atom is bonded, andthe benzene ring-containing group to which R^(b2) is bonded have astructure in which R^(b2) and Ar are not bonded at the para positionwith respect to the bonding position at which the N atom is bonded.

When the compound according to one aspect of the invention is used as adopant material for an emitting layer that forms an organic EL device,the emission wavelength may increase, and the blue chromaticity of theresulting light may decrease if an alkyl group or an aryl group isbonded at the para position with respect to the bonding position atwhich the N atom is bonded. Since deep (short-wavelength) blue light issuitable for various applications that utilize an organic EL device, itis preferable that an alkyl group, an aryl group, or the like is absentat the para position with respect to the bonding position at which the Natom is bonded.

Note that the benzene ring-containing group may be substituted withR^(b1) and Ar at para positions.

In the formula (1), it is preferable that Ar be bonded at the paraposition with respect to R^(a). Specifically, it is preferable that thebenzene ring-containing group to which R^(b1) is bonded be representedby the following formula (10), and the benzene ring-containing group towhich R^(b2) is bonded be represented by the following formula (11). Inthis case, it is considered that the molecular arrangement of thecompound according to one aspect of the invention in an organic film isoptimized or nearly optimized, and an energy transfer from an emittinglayer and the like are optimized or nearly optimized when the compoundaccording to one aspect of the invention is used as a dopant materialfor an emitting layer that forms an organic EL device, so that theluminous efficiency is improved.

Ar, R^(a), R^(b1), R^(b2), and x in the formulas (10) and (11) are thesame as defined for the formula (1).

It is preferable that R^(b3) and R^(b4) in the formula (1) not be bondedat the para position with respect to the bonding position at which the Natom is bonded. Specifically, it is preferable that R^(b3) and R^(b4) bebonded at the meta position or the ortho position with respect to thebonding position at which the N atom is bonded, and it is preferablethat R^(b3) and R^(b4) be bonded at the ortho position with respect tothe bonding position at which the N atom is bonded. Specifically, it ispreferable that the benzene ring-containing group to which R^(b3) isbonded be represented by the following formula (12), and the benzenering-containing group to which R^(b4) is bonded be represented by thefollowing formula (13).

R^(b3) and R^(b4) in the formulas (12) and (13) are the same as definedfor the formula (1).

R^(b3) and R^(b4) are independently a substituted or unsubstituted alkylgroup including 1 to 15 carbon atoms, or a substituted or unsubstitutedcycloalkyl group including 3 to 15 carbon atoms, and z1 areindependently an integer from 0 to 4.

It is preferable that R^(a) be independently a substituted orunsubstituted alkyl group including 1 to 6 carbon atoms.

It is preferable that R^(b1) to R^(b4) be independently a group otherthan an electron-withdrawing group. Specifically, it is preferable thatR^(b1) to R^(b4) be independently a substituted or unsubstituted alkylgroup including 1 to 15 carbon atoms, a substituted or unsubstitutedcycloalkyl group including 3 to 15 carbon atoms, a substituted orunsubstituted alkylsilyl group including 1 to 45 carbon atoms, asubstituted or unsubstituted arylsilyl group including 6 to 50 carbonatoms, a substituted or unsubstituted alkoxy group including 1 to 15carbon atoms, a substituted or unsubstituted aryloxy group including 6to 30 ring carbon atoms, a substituted or unsubstituted alkylthio groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted arylthiogroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms.

It is more preferable that R^(b1) to R^(b4) be independently asubstituted or unsubstituted alkyl group including 1 to 15 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 15 carbonatoms, a substituted or unsubstituted alkylsilyl group including 1 to 45carbon atoms, a substituted or unsubstituted arylsilyl group including 6to 50 carbon atoms, or a substituted or unsubstituted aryl groupincluding 6 to 30 ring carbon atoms.

It is preferable that R^(c1) to R^(c10) be a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, or a substituted or unsubstituted arylsilyl group including 6 to50 carbon atoms, and more preferably a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms.

It is preferable that the compound according to one aspect of theinvention be a compound represented by the following formula (4-2) or(5-2).

Each group in the formulas (4-2) and (5-2) is the same as defined above.

The compound may be produced using the method described in the examples.The compound according to the invention may be synthesized in accordancewith the reaction described in the examples using an appropriate knownalternative reaction or raw material taking account of the targetproduct.

The term “hydrogen atom” used herein includes isotopes of hydrogen thatdiffer in the number of neutrons (i.e., protium, deuterium, andtritium).

The term “number of ring carbon atoms” used herein refers to the numberof carbon atoms among the atoms that form the ring of a compoundincluding a structure in which atoms are bonded in a ring-like manner(e.g., monocyclic compound, fused ring compound, bridged compound,carbocyclic compound, and heterocyclic compound). When the ring issubstituted with a substituent, the number of ring carbon atoms excludesthe number of carbon atoms included in the substituent. The abovedefinition is applied to the term “number of ring carbon atoms” unlessotherwise specified. For example, the number of ring carbon atoms of abenzene ring is 6, the number of ring carbon atoms of a naphthalene ringis 10, the number of ring carbon atoms of a pyridinyl group is 5, andthe number of ring carbon atoms of a furanyl group is 4. For example,when a benzene ring or a naphthalene ring is substituted with an alkylgroup, the number of ring carbon atoms excludes the number of carbonatoms of the alkyl group. For example, when a fluorene ring issubstituted with a fluorene ring (including a spirofluorene ring), thenumber of ring carbon atoms excludes the number of carbon atoms of thefluorene ring that is bonded as a substituent.

The term “number of ring atoms” used herein refers to the number ofatoms that form the ring of a compound including a structure (e.g.,monocyclic ring, fused ring, and ring assembly) in which atoms arebonded in a ring-like manner (e.g., monocyclic compound, fused ringcompound, bridged compound, carbocyclic compound, and heterocycliccompound). The number of ring atoms excludes the number of atoms that donot form the ring (e.g., a hydrogen atom that is bonded to (terminates)an atom that forms the ring), and the number of atoms included in asubstituent when the ring is substituted. The above definition isapplied to the term “number of ring atoms” unless otherwise specified.For example, the number of ring atoms of a pyridine ring is 6, thenumber of ring atoms of a quinazoline ring is 10, and the number of ringatoms of a furan ring is 5. The number of ring atoms excludes the numberof hydrogen atoms that are bonded to the carbon atoms of a pyridine ringor a quinazoline ring, and the number of atoms that are included in asubstituent. For example, when a fluorene ring is substituted with afluorene ring (including a spirofluorene ring), the number of ring atomsexcludes the number of atoms of the fluorene ring that is bonded as asubstituent.

The expression “XX to YY carbon atoms” used in connection with theexpression “substituted or unsubstituted ZZ group including XX to YYcarbon atoms” refers to the number of carbon atoms when the ZZ group isunsubstituted, and excludes the number of carbon atoms included in asubstituent when the ZZ group is substituted. Note that “YY” is largerthan “XX”, and “XX” and “YY” are independently an integer equal to orlarger than 1.

The expression “XX to YY atoms” used in connection with the expression“substituted or unsubstituted ZZ group including XX to YY atoms” refersto the number of atoms when the ZZ group is unsubstituted, and excludesthe number of atoms included in a substituent when the ZZ group issubstituted. Note that “YY” is larger than “XX”, and “XX” and “YY” areindependently an integer equal to or larger than 1.

The term “unsubstituted” used in connection with the expression“substituted or unsubstituted” means that the group is not substitutedwith a substituent (i.e., a hydrogen atom is bonded).

Each group that is or may be included in each formula is described indetail below.

Examples of the alkyl group include a methyl group, an ethyl group, apropyl group, an isopropyl group, an n-butyl group, an s-butyl group, anisobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, ann-heptyl group, an n-octyl group, and the like.

The number of carbon atoms of the alkyl group is preferably 1 to 10, andmore preferably 1 to 6. A methyl group, an ethyl group, a propyl group,an isopropyl group, an n-butyl group, an s-butyl group, an isobutylgroup, a t-butyl group, an n-pentyl group, and an n-hexyl group arepreferable as the alkyl group.

Examples of the cycloalkyl group include a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, a4-methylcyclohexyl group, an adamantyl group, a norbornyl group, and thelike. The number of ring carbon atoms of the cycloalkyl group ispreferably 3 to 10, more preferably 3 to 8, and still more preferably 5to 8. The number of ring carbon atoms of the cycloalkyl group may be 3to 6.

Examples of the aryl group include a phenyl group, a naphthyl group, ananthryl group, a phenanthryl group, a naphthacenyl group, a pyrenylgroup, a chrysenyl group, a benzo[c]phenanthryl group, abenzo[g]chrysenyl group, a triphenylenyl group, a fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a biphenylyl group, ano-terphenyl group, an m-terphenyl group, a p-terphenyl group, afluoranthenyl group, and the like.

The number of ring carbon atoms of the aryl group is preferably 6 to 20,and more preferably 6 to 12. A phenyl group and a biphenyl group areparticularly preferable as the aryl group.

The alkylsilyl group is represented by —SiY₃. Examples of Y include thegroups mentioned above in connection with the alkyl group. Examples ofthe alkylsilyl group include a trimethylsilyl group, a triethylsilylgroup, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, apropyldimethylsilyl group, a triisopropylsilyl group, and the like.

The arylsilyl group is a silyl group that is substituted with one tothree aryl groups. Examples of the aryl group include the groupsmentioned above in connection with the aryl group. The arylsilyl groupmay be further substituted with an alkyl group mentioned above. Examplesof the arylsilyl group include a triphenylsilyl group, aphenyldimethylsilyl group, and the like.

The alkoxy group is represented by —OY. Examples of Y include the groupsmentioned above in connection with the alkyl group. Examples of thealkoxy group include a methoxy group and an ethoxy group.

The aryloxy group is represented by —OZ. Examples of Z include thegroups mentioned above in connection with the aryl group. Examples ofthe aryloxy group include a phenoxy group.

The alkylthio group is represented by —SY. Examples of Y include thegroups mentioned above in connection with the alkyl group.

The arylthio group is represented by —SZ. Examples of Z include thegroups mentioned above in connection with the aryl group.

The arylamino group is represented by —NZ₂. Examples of Z include thegroups mentioned above in connection with the aryl group.

Examples of the heteroaryl group include a pyrrolyl group, a triazinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridinyl group, anindolyl group, an isoindolyl group, an imidazolyl group, a furyl group,a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group,a dibenzothiophenyl group, a quinolyl group, an isoquinolyl group, aquinoxalinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenothiazinyl group, a phenoxadinyl group, an oxazolyl group, anoxadiazolyl group, a furazanyl group, a thienyl group, a benzothiophenylgroup, and the like.

The number of ring atoms of the heteroaryl group is preferably 5 to 20,and more preferably 5 to 14.

Adibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl groupare preferable as the heteroaryl group, and a 1-dibenzofuranyl group, a2-dibenzofuranyl group, a 3-dibenzofuranyl group, a 4-dibenzofuranylgroup, a 1-dibenzothiophenyl group, a 2-dibenzothiophenyl group, a3-dibenzothiophenyl group, and a 4-dibenzothiophenyl group are morepreferable as the heteroaryl group.

The term “carbazolyl group” used herein also includes the groupsrespectively having the following structures.

The term “heteroaryl group” used herein also includes the groupsrespectively having the following structures.

wherein X and Y are independently an oxygen atom, a sulfur atom, anitrogen atom, or an —NH— group.

Examples of the halogen atom include a fluorine atom, a chlorine atom, abromine atom, an iodine atom, and the like. Among these, a fluorine atomis preferable.

Examples of a substituent when the expression “substituted orunsubstituted” is used include those mentioned above.

The substituent may be further substituted with another substituentmentioned above. A plurality of substituents may be bonded to form aring.

Examples of the compound according to one aspect of the inventioninclude the following compounds.

The compound according to one aspect of the invention may be used as amaterial for an organic electroluminescence (EL) device (preferably anemitting material for an organic EL device, and more preferably a dopant(dopant material)).

An organic EL device according to one aspect of the invention includes acathode, an anode, and one or more organic thin film layers that areprovided between the cathode and the anode, the one or more organic thinfilm layers including at least an emitting layer, and at least oneorganic thin film layer included in the one or more organic thin filmlayers including the compound represented by the formula (1) eitheralone or as a component of a mixture.

It is preferable that the emitting layer include the compound. Theemitting layer may include only the compound, or may include thecompound as a host or a dopant.

In the organic EL device according to one aspect of the invention, it ispreferable that at least one organic thin film layer included in the oneor more organic thin film layers include the compound, and at least onecompound among an anthracene derivative represented by the followingformula (5) and a pyrene derivative represented by the following formula(6). It is preferable that the emitting layer include the compound as adopant, and include the anthracene derivative as a host.

The anthracene derivative is a compound represented by the followingformula (5).

Ar¹¹ and Ar¹² in the formula (5) are independently a substituted orunsubstituted monocyclic group including 5 to 50 ring atoms, asubstituted or unsubstituted fused ring group including 8 to 50 ringatoms, or a group formed by a combination of the monocyclic group andthe fused ring group.

R¹⁰¹ to R¹⁰⁸ are independently an atom or a group selected from thegroup consisting of a hydrogen atom, a substituted or unsubstitutedmonocyclic group including 5 to 50 (preferably 5 to 30, more preferably5 to 20, and still more preferably 5 to 12) ring atoms, a substituted orunsubstituted fused ring group including 8 to 50 (preferably 8 to 30,more preferably 8 to 20, and still more preferably 8 to 14) ring atoms,a group formed by a combination of the monocyclic group and the fusedring group, a substituted or unsubstituted alkyl group including 1 to 50(preferably 1 to 20, more preferably 1 to 10, and still more preferably1 to 6) carbon atoms, a substituted or unsubstituted cycloalkyl groupincluding 3 to 50 (preferably 3 to 20, more preferably 3 to 10, andstill more preferably 5 to 8) ring carbon atoms, a substituted orunsubstituted alkoxy group including 1 to 50 (preferably 1 to 20, morepreferably 1 to 10, and still more preferably 1 to 6) carbon atoms, asubstituted or unsubstituted aralkyl group including 7 to 50 (preferably7 to 20, and more preferably 7 to 14) carbon atoms, a substituted orunsubstituted aryloxy group including 6 to 50 (preferably 6 to 20, andmore preferably 6 to 12) ring carbon atoms, a substituted orunsubstituted silyl group, a halogen atom, and a cyano group.

It is preferable that all of R¹⁰¹ to R¹⁰⁸ be a hydrogen atom, or eitherR¹⁰¹ or R¹⁰⁸, either R¹⁰⁴ or R¹⁰⁶, both R¹⁰¹ and R¹⁰⁶, or both R¹⁰⁸ andR¹⁰⁴ be a group selected from the group consisting of a monocyclic groupincluding 5 to 50 ring atoms (preferably a phenyl group, a biphenylylgroup, and a terphenylyl group), a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms (preferably a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, an s-butyl group, and a t-butyl group), and asubstituted silyl group (preferably a trimethylsilyl group), and it ismore preferable that all of R¹⁰¹ to R¹⁰⁸ be a hydrogen atom.

The term “monocyclic group” used herein in connection with the formula(5) refers to a group that includes only a ring structure that does nothave a fused ring structure.

Specific examples of a preferable monocyclic group including 5 to 50ring atoms include an aromatic group (e.g., phenyl group, biphenylylgroup, terphenylyl group, and quaterphenylyl group) and a heterocyclicgroup (e.g., pyridyl group, pyrazyl group, pyrimidyl group, triazinylgroup, furyl group, and thienyl group).

Among these, a phenyl group, a biphenylyl group, and a terphenylyl groupare preferable.

The term “fused ring group” used herein in connection with the formula(5) refers to a group in which two or more ring (cyclic) structures arefused.

Specific examples of a preferable fused ring group including 8 to 50ring atoms include a fused aromatic ring group (e.g., naphthyl group,phenanthryl group, anthryl group, chrysenyl group, benzanthryl group,benzophenanthryl group, triphenylenyl group, benzochrysenyl group,indenyl group, fluorenyl group, benzofluorenyl group, dibenzofluorenylgroup, fluoranthenyl group, and benzofluoranthenyl group) and a fusedheterocyclic group (e.g., benzofuranyl group, benzothiophenyl group,indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolylgroup, quinolyl group, and phenanthrolinyl group).

The fluorenyl group may be substituted with one or two substituents atthe position 9. Examples of the substituent include an alkyl group, anaryl group, an alkylsilyl group, an arylsilyl group, an alkoxy group,and the like. Specific examples of such a substituted fluorenyl groupinclude a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group,and the like. The term “fluorenyl group” used hereinafter includes sucha substituted fluorenyl group unless otherwise specified.

A naphthyl group, a phenanthryl group, an anthryl group, a fluorenylgroup (e.g., 9,9-dimethylfluorenyl group), a fluoranthenyl group, abenzanthryl group, a dibenzothiophenyl group, a dibenzofuranyl group,and a carbazolyl group are preferable as the fused ring group.

Specific examples of the alkyl group, the cycloalkyl group, the alkoxygroup, the alkyl moiety and the aryl moiety of the aralkyl group, thearyloxy group, the substituted silyl group (alkylsilyl group andarylsilyl group), and the halogen atom mentioned above in connectionwith the formula (5) include those (group and substituent) mentionedabove in connection with the formula (1).

The aralkyl group is represented by —Y—Z. Examples of Y include alkylenegroups that correspond to those mentioned above in connection with thealkyl group. Examples of Z include those mentioned above in connectionwith the aryl group. The number of carbon atoms of the aralkyl group ispreferably 7 to 50 (i.e., the number of carbon atoms of the aryl moietyis 6 to 49 (preferably 6 to 30, more preferably 6 to 20, andparticularly preferably 6 to 12), and the number of carbon atoms of thealkyl moiety is 1 to 44 (preferably 1 to 30, more preferably 1 to 20,still more preferably 1 to 10, and particularly preferably 1 to 6)).Examples of the aralkyl group include a benzyl group, a phenylethylgroup, and a 2-phenylpropan-2-yl group.

A substituent that may substitute Ar¹¹, Ar¹², and R¹ to R⁸ is preferablya monocyclic group, a fused ring group, an alkyl group, a cycloalkylgroup, a silyl group, an alkoxy group, a cyano group, or a halogen atom(particularly a fluorine atom), and particularly preferably a monocyclicgroup or a fused ring group. Specific examples of a preferablesubstituent include those mentioned above.

Note that a substituent that may substitute Ar¹¹ and Ar¹² is preferablythe monocyclic group or the fused ring group mentioned above.

The anthracene derivative represented by the formula (5) is preferablyan anthracene derivative among the following anthracene derivatives (A),(B), and (C). The anthracene derivative is selected taking account ofthe configuration and the desired properties of the organic EL device.

Anthracene Derivative (A)

The anthracene derivative (A) is the anthracene derivative representedby the formula (5) wherein Ar¹¹ and Ar¹² are independently a substitutedor unsubstituted fused ring group including 8 to 50 ring atoms. Ar¹¹ andAr¹² in the anthracene derivative may be either identical or different.

The anthracene derivative (A) is preferably the anthracene derivativerepresented by the formula (5) wherein Ar¹¹ and Ar¹² are a substitutedor unsubstituted fused ring group and differ from each other (includinga difference in the position at which the anthracene ring is bonded).Specific examples of a preferable fused ring group include thosementioned above. A naphthyl group, a phenanthryl group, a benzanthrylgroup, a fluorenyl group (e.g., 9,9-dimethylfluorenyl group), and adibenzofuranyl group are preferable as the fused ring group.

Anthracene Derivative (B)

The anthracene derivative (B) is the anthracene derivative representedby the formula (5) wherein one of Ar¹¹ and Ar¹² is a substituted orunsubstituted monocyclic group including 5 to 50 ring atoms, and theother of Ar¹¹ and Ar¹² is a substituted or unsubstituted fused ringgroup including 8 to 50 ring atoms.

Examples of a preferable anthracene derivative (B) include theanthracene derivative represented by the formula (5) wherein Ar¹² is anaphthyl group, a phenanthryl group, a benzanthryl group, a fluorenylgroup (e.g., 9,9-dimethylfluorenyl group), or a dibenzofuranyl group,and Ar¹¹ is an unsubstituted phenyl group, or a phenyl group substitutedwith a monocyclic group or a fused ring group (e.g., phenyl group,biphenyl group, naphthyl group, phenanthryl group, fluorenyl group(e.g., 9,9-dimethylfluorenyl group), or dibenzofuranyl group). Specificexamples of a preferable monocyclic group and a preferable fused ringgroup include those mentioned above.

Further examples of a preferable anthracene derivative (B) include theanthracene derivative represented by the formula (5) wherein Ar¹² is asubstituted or unsubstituted fused ring group including 8 to 50 ringatoms, and Ar¹¹ is an unsubstituted phenyl group. In this case, aphenanthryl group, a fluorenyl group (e.g., 9,9-dimethylfluorenylgroup), a dibenzofuranyl group, and a benzanthryl group are particularlypreferable as the fused ring group.

Anthracene Derivative (C)

The anthracene derivative (C) is the anthracene derivative representedby the formula (5) wherein Ar¹¹ and Ar¹² are independently a substitutedor unsubstituted monocyclic group including 5 to 50 ring atoms.

Examples of a preferable anthracene derivative (C) include theanthracene derivative represented by the formula (5) wherein Ar¹¹ andAr¹² are a substituted or unsubstituted phenyl group. Examples of a morepreferable anthracene derivative (C) include the anthracene derivativerepresented by the formula (5) wherein Ar¹¹ is an unsubstituted phenylgroup, and Ar¹² is a phenyl group substituted with a monocyclic group ora fused ring group, and the anthracene derivative represented by theformula (5) wherein Ar¹¹ and Ar¹² are independently a phenyl groupsubstituted with a monocyclic group or a fused ring group.

Specific examples of a preferable monocyclic group and a preferablefused ring group as a substituent include those mentioned above. Themonocyclic group used as a substituent is more preferably a phenyl groupor a biphenyl group, and the fused ring group used as a substituent ismore preferably a naphthyl group, a phenanthryl group, a fluorenyl group(e.g., 9,9-dimethylfluorenyl group), a dibenzofuranyl group, or abenzanthryl group.

Specific examples of the anthracene derivative represented by theformula (5) include the following compounds.

The pyrene derivative is represented by the following formula (6).

Ar¹¹¹ and Ar²²² in the formula (6) are independently a substituted orunsubstituted aryl group including 6 to 30 ring carbon atoms.

L¹ and L² are independently a substituted or unsubstituted divalentarylene group including 6 to 30 ring carbon atoms, or a heterocyclicgroup.

m is an integer from 0 to 1, n is an integer from 1 to 4, s is aninteger from 0 to 1, and t is an integer from 0 to 3.

L¹ or Ar¹¹¹ is bonded to one of the positions 1 to 5 of the pyrene ring,and L² or Ar²²² is bonded to one of the positions 6 to 10 of the pyrenering.

L¹ and L² in the formula (6) are preferably a substituted orunsubstituted phenylene group, a substituted or unsubstitutedbiphenylene group, a substituted or unsubstituted naphthylene group, asubstituted or unsubstituted terphenylene group, a substituted orunsubstituted fluorenylene group, or a divalent aryl group formed by acombination of these groups.

Examples of a substituent include those mentioned above in connectionwith the formula (1). A substituent that may substitute L¹ and L² ispreferably an alkyl group including 1 to 20 carbon atoms.

m in the formula (6) is preferably an integer from 0 to 1. n in theformula (6) is preferably an integer from 1 to 2. s in the formula (6)is preferably an integer from 0 to 1. t in the formula (6) is preferablyan integer from 0 to 2.

Examples of the aryl group represented by Ar¹¹¹ and Ar²²² include thosementioned above in connection with the formula (1). Ar¹¹¹ and Ar²²² arepreferably a substituted or unsubstituted aryl group including 6 to 20ring carbon atoms, and more preferably a substituted or unsubstitutedaryl group including 6 to 16 ring carbon atoms. Specific examples of apreferable aryl group include a phenyl group, a naphthyl group, aphenanthryl group, a fluorenyl group, a biphenyl group, an anthrylgroup, and a pyrenyl group.

When the organic thin film layer includes the compound represented bythe formula (1) as a dopant, the content of the compound represented bythe formula (1) in the organic thin film layer is preferably 0.1 to 20mass %, and more preferably 1 to 10 mass %.

The compound represented by the formula (1) and the anthracenederivative or the pyrene derivative may also be used for ahole-injecting layer, a hole-transporting layer, an electron-injectinglayer, or an electron-transporting layer in addition to the emittinglayer.

When the organic EL device according to one aspect of the inventionincludes a plurality of organic thin film layers, the organic EL devicemay have a stacked structure such as an (anode/hole-injectinglayer/emitting layer/cathode) stacked structure, an (anode/emittinglayer/electron-injecting layer/cathode) stacked structure, an(anode/hole-injecting layer/emitting layer/electron-injectinglayer/cathode) stacked structure, or an (anode/hole-injectinglayer/hole-transporting layer/emitting layer/electron-injectinglayer/cathode) stacked structure.

When the organic EL device includes a plurality of organic thin filmlayers, a decrease in luminance or lifetime due to quenching can beprevented. An emitting material, a doping material, a hole-injectingmaterial, and an electron-injecting material may optionally be used incombination. The luminance or the luminous efficiency may be improveddepending on the doping material. The hole-injecting layer, the emittinglayer, and the electron-injecting layer may respectively include two ormore layers. When the hole-injecting layer includes two or more layers,a layer into which holes are injected from the electrode is referred toas “hole-injecting layer”, and a layer that receives holes from thehole-injecting layer, and transports the holes to the emitting layer isreferred to as “hole-transporting layer”. Likewise, when theelectron-injecting layer includes two or more layers, a layer into whichelectrons are injected from the electrode is referred to as“electron-injecting layer”, and a layer that receives electrons from theelectron-injecting layer, and transports the electrons to the emittinglayer is referred to as “electron-transporting layer”. Each layer isselected taking account of the energy level of the material, the heatresistance of the material, the adhesion of the material to an organiclayer or a metal electrode, and the like.

Examples of a material other than the compounds represented by theformulas (5) and (6) that may be used for the emitting layer togetherwith the compound represented by the formula (1) include, but are notlimited to, a fused polycyclic aromatic compound such as naphthalene,phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene,chrysene, decacyclene, coronene, tetraphenylcyclopentadiene,pentaphenylcyclopentadiene, fluorene, and spirofluorene, and aderivative thereof, an organic metal complex such astris(8-quinolinolate)aluminum, a triarylamine derivative, a styrylaminederivative, a stilbene derivative, a coumarin derivative, a pyranderivative, an oxazone derivative, a benzothiazole derivative, abenzoxazole derivative, a benzimidazole derivative, a pyrazinederivative, a cinnamate derivative, a diketopyrrolopyrrole derivative,an acridone derivative, a quinacridone derivative, and the like.

The hole-injecting layer is a layer that includes a substance that has ahigh hole-injecting capability. Examples of the substance that has ahigh hole-injecting capability include molybdenum oxide, titanium oxide,vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide,zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungstenoxide, manganese oxide, an aromatic amine compound, a polymer compound(e.g., oligomer, dendrimer, and polymer), and the like.

The hole-transporting layer is a layer that includes a substance thathas a high hole-transporting capability. An aromatic amine compound, acarbazole derivative, an anthracene derivative, and the like may be usedto form the hole-transporting layer. A polymer compound such aspoly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) mayalso be used to form the hole-transporting layer. Note that anothersubstance may also be used as long as the hole-transporting capabilityof the substance is higher than the electron-transporting capability.The layer that includes a substance that has a high hole-transportingcapability may be a single layer, or may have a structure in which twoor more layers formed of the substance that has a high hole-transportingcapability are stacked.

The electron-transporting layer is a layer that includes a substancethat has a high electron-transporting capability. Theelectron-transporting layer may be formed using 1) a metal complex suchas an aluminum complex, a beryllium complex, or a zinc complex, 2) aheteroaromatic compound such as an imidazole derivative, a benzimidazolederivative, an azine derivative, a carbazole derivative, or aphenanthroline derivative, or 3) a polymer compound.

The electron-injecting layer is a layer that includes a substance thathas a high electron-injecting capability. The electron-injecting layermay be formed using an alkali metal, an alkaline-earth metal, or acompound thereof (e.g., lithium (Li), lithium fluoride (LiF), cesiumfluoride (CsF), calcium fluoride (CaF₂), and lithium oxide (LiO_(x))).

In the organic EL device according to one aspect of the invention, theemitting layer may include at least one of the emitting material, thedoping material, the hole-injecting material, the hole-transportingmaterial, and the electron-injecting material in addition to at leastone compound represented by the formula (1). A protective layer may beprovided on the surface of the organic EL device, or the entire organicEL device may be protected with silicon oil, a resin, or the like sothat the resulting organic EL device exhibits improved stability againsttemperature, humidity, atmosphere, and the like.

The anode is preferably formed on the substrate using a metal, an alloy,or an electrically conductive compound having a large work function(e.g., 4.0 eV or more), or a mixture thereof, for example. Specificexamples of such a material include indium tin oxide (ITO), indium tinoxide that includes silicon or silicon oxide, indium zinc oxide,tungsten oxide, indium oxide that includes zinc oxide, graphene, and thelike. Gold (Au), platinum (Pt), a nitride of a metal material (e.g.,titanium nitride), and the like may also be used.

The cathode is preferably formed using a metal, an alloy, or anelectrically conductive compound having a small work function (e.g., 3.8eV or less), or a mixture thereof, for example. Specific examples ofsuch a cathode material include the elements that belong to Group 1 or 2in the periodic table (i.e., an alkali metal such as lithium (Li) andcesium (Cs), and an alkaline-earth metal such as magnesium (Mg)) and analloy thereof (e.g., MgAg and AlLi), a rare-earth metal and an alloythereof, and the like.

The anode and the cathode may optionally include two or more layers.

It is desirable that at least one side of the organic EL device besufficiently transparent within the emission wavelength region of thedevice so that the device efficiently emits light. It is desirable thatthe substrate also be transparent. A transparent electrode is formed bydeposition, sputtering, or the like using the above conductive materialso that a given translucency is achieved. It is desirable that theemitting-side electrode have a light transmittance of 10% or more.

A glass substrate, a quartz substrate, a plastic substrate, or the likemay be used as the substrate, for example. A flexible substrate may alsobe used. The term “flexible substrate” used herein refers to a substratethat can be bent (i.e., is flexible). Examples of such a flexiblesubstrate include a plastic substrate formed of a polycarbonate orpolyvinyl chloride, and the like.

Each layer of the organic EL device may be formed using a dryfilm-forming method such as a vacuum deposition method, a sputteringmethod, a plasma method, or an ion plating method, or a wet film-formingmethod such as a spin coating method, a dipping method, or a flowcoating method. The thickness of each layer is not particularly limitedas long as each layer has an appropriate thickness. If the thickness ofeach layer is too large, a high applied voltage may be required toobtain a constant optical output (i.e., deterioration in efficiency mayoccur). If the thickness of each layer is too small, pinholes or thelike may occur, and sufficient luminance may not be obtained even if anelectric field is applied. The thickness of each layer is normally 5 nmto 10 μm, and preferably 10 nm to 0.2 μm.

When using a wet film-forming method, the material for forming eachlayer is dissolved or dispersed in an appropriate solvent (e.g.,ethanol, chloroform, tetrahydrofuran, or dioxane), and a thin film isformed using the solution or the dispersion. The solvent is notparticularly limited.

An organic EL material-containing solution that includes the compoundrepresented by the formula (1) (i.e., organic EL material) and a solventmay be used as a solution that is suitable for the wet film-formingmethod.

It is preferable that the organic EL material include a host materialand a dopant material, the dopant material be the compound representedby the formula (1), and the host material be at least one compoundselected from the compound represented by the formula (5).

An appropriate resin or an appropriate additive may be added to eachorganic thin film layer in order to improve the film-forming capabilityand prevent the occurrence of pinholes, for example.

The organic EL device according to one aspect of the invention may beused as a planar emitting device (e.g., a flat panel display used for awall TV), a backlight of a copier, a printer, or a liquid crystaldisplay, a light source of an instrument (meter), a signboard, a markerlamp (light), and the like. The compound according to one aspect of theinvention may also be used in the fields of an electrophotographicphotoreceptor, a photoelectric conversion device, a solar cell, an imagesensor, and the like in addition to the field of an organic EL device.

EXAMPLES

The invention is further described below by way of examples. Note thatthe invention is not limited to the following examples.

Example 1: Synthesis of Compound 1

A compound 1 was synthesized according to the following scheme.

(1-1) Synthesis of 2-methyl-5-phenylaniline

A mixture of 5-bromo-2-methylaniline (10.0 g), phenylboronic acid (8.52g), tetrakis(triphenylphosphine)palladium (0) (1.86 g), a 2 M sodiumcarbonate aqueous solution (80.6 mL), and 1,2-dimethoxyethane (DME) (135mL) was refluxed for 5 hours in an argon atmosphere. The resultingreaction mixture was cooled to room temperature, and extracted withdichloromethane. The organic layer was washed with water, and dried overanhydrous magnesium sulfate, and the solvent was evaporated underreduced pressure. The resulting crude 2-methyl-5-phenylaniline was useddirectly for the subsequent step.

(1-2) Synthesis of 2-methyl-N-(o-tolyl)-5-phenylaniline

A mixture of crude 2-methyl-5-phenylaniline obtained by the step (1-1),2-bromotoluene (7.35 g), tris(dibenzylideneacetone)dipalladium(0) (0.98g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (1.67 g), sodiumt-butoxide (7.75 g), and toluene (270 g) was refluxed for 5 hours in anargon atmosphere. The resulting reaction mixture was cooled to roomtemperature. After the addition of water, the mixture was extracted withtoluene. The organic layer was washed with a saturated sodium chloridesolution, and dried over anhydrous magnesium sulfate, and the solventwas evaporated under reduced pressure. The residue was purified bysilica gel column chromatography to obtain2-methyl-N-(o-tolyl)-5-phenylaniline (10.17 g). The yield achieved bythe steps (1-1) and (1-2) was 69%.

(1-3) Synthesis of Compound 1

A mixture of 1,6-dibromopyrene (5.82 g),2-methyl-N-(o-tolyl)-5-phenylaniline (10.17 g) obtained by the step(1-2), tris(dibenzylideneacetone)dipalladium(0) (0.89 g),tri-t-butylphosphine tetrafluoroborate (0.56 g), sodium t-butoxide (6.22g), and toluene (162 mL) was refluxed for 7 hours in an argonatmosphere. The resulting reaction mixture was cooled to roomtemperature. After the addition of water, the mixture was extracted withtoluene. The organic layer was washed with a saturated sodium chloridesolution, and dried over anhydrous magnesium sulfate, and the solventwas evaporated under reduced pressure. The residue was purified bysilica gel column chromatography and recrystallization to obtain acompound 1 (0.29 g). The yield was 3%. It was confirmed by mass spectrumanalysis that the compound 1 was obtained. The compound 1 had amolecular weight of 744.35 (m/e=744).

Example 2: Synthesis of Compound 2

A compound 2 was synthesized according to the following scheme.

(2-1) Synthesis of 2-bromo-4-iodotoluene

A mixture of 3-bromo-4-methylaniline (18.6 g) and 6 M hydrochloric acid(80 mL) was cooled to −5° C. in an argon atmosphere. After the dropwiseaddition of an aqueous solution (15 mL) of sodium nitrite (7.35 g) whilemaintaining the mixture at 0° C. or less, the resulting mixture wasstirred at −8° C. for 45 minutes. Potassium iodide (33.2 g) was added tothe mixture over 3 hours while maintaining the mixture at 0° C. or less.The resulting reaction mixture was returned to room temperature. Afterthe addition of a 10% sodium hydrogen sulfite aqueous solution (50 mL),the mixture was extracted with diethyl ether. The organic layer waswashed with a 10% sodium hydrogen sulfite aqueous solution, and driedover anhydrous magnesium sulfate, and the solvent was evaporated underreduced pressure. The residue was purified by silica gel columnchromatography to obtain 2-bromo-4-iodotoluene (14.5 g). The yield was49%.

(2-2) Synthesis of 2-bromo-1-methyl-4-phenylbenzene

A mixture of 2-bromo-4-iodotoluene (14.5 g) obtained by the step (2-1),phenylboronic acid (6.35 g), tetrakis(triphenylphosphine)palladium (0)(1.69 g), potassium carbonate (20.2 g), 1,4-dioxane (117 mL), and water(13 mL) was refluxed for 3 hours in an argon atmosphere. The resultingreaction mixture was returned to room temperature, and extracted withdichloromethane. The organic layer was washed with a saturated sodiumchloride solution, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel column chromatographyto obtain 2-bromo-1-methyl-4-phenylbenzene (8.6 g). The yield was 71%.

(2-3) Synthesis of N,N-bis(2-methyl-5-phenylphenyl)amine

A mixture of crude 2-methyl-5-phenylaniline produced from 6.59 g of5-bromo-2-methylaniline in the same manner as in the step (1-1) ofExample 1, 2-bromo-1-methyl-4-phenylbenzene (7.0 g) obtained by the step(2-2), tris(dibenzylideneacetone)dipalladium(0) (0.65 g), BINAP (1.1 g),sodium t-butoxide (5.1 g), and toluene (100 mL) was refluxed for 4.5hours in an argon atmosphere. The resulting reaction mixture was cooledto room temperature, and filtered through celite, and the solvent wasevaporated under reduced pressure. The residue was purified by silicagel column chromatography to obtainN,N-bis(2-methyl-5-phenylphenyl)amine (6.03 g). The yield was 61%.

(2-4) Synthesis of Compound 2

A mixture of 1,6-dibromopyrene (5.09 g),N,N-bis(2-methyl-5-phenylphenyl)amine (11.87 g) obtained by the step(2-3), tris(dibenzylideneacetone)dipalladium(0) (0.78 g),tri-t-butylphosphine tetrafluoroborate (0.82 g), sodium t-butoxide (4.08g), and toluene (150 mL) was refluxed for 6.5 hours in an argonatmosphere. After the addition oftris(dibenzylideneacetone)dipalladium(0) (0.16 g) andtri-t-butylphosphine tetrafluoroborate (0.16 g) to the resultingreaction mixture, the resulting mixture was refluxed for 5 hours. Theresulting reaction mixture was returned to room temperature. After theaddition of water, a solid produced in the system was filtered off,washed with water and methanol, and purified by silica gel columnchromatography and recrystallization to obtain a compound 2 (2.18 g).The yield was 17%. It was confirmed by mass spectrum analysis that thecompound 2 was obtained. The compound 2 had a molecular weight of 896.41(m/e=896).

Example 3: Synthesis of Compound 3

A compound 3 was obtained in the same manner as in Example 1, exceptthat 3-bromo-2-methylaniline was used instead of5-bromo-2-methylaniline. It was confirmed by mass spectrum analysis thatthe compound 3 was obtained. The compound 3 had a molecular weight of744.35 (m/e=744).

Example 4: Synthesis of Compound 4

A compound 4 was synthesized according to the following scheme.

A mixture of 1,6-dibromo-3,8-diisopropylpyrene (18.4 g),2-methyl-N-(o-tolyl)-5-phenylaniline (10.17 g) obtained by the step(1-2), palladium(II) acetate (0.37 g), tri-t-butylphosphine (0.67 g),sodium t-butoxide (9.6 g), and xylene (430 mL) was stirred at 105° C.for 21.5 hours in an argon atmosphere. The resulting reaction mixturewas cooled to room temperature. After the addition of methanol, theresulting mixture was stirred for 3 hours. A solid that precipitated wasfiltered off, and purified by silica gel column chromatography andrecrystallization to obtain a compound 4 (13.4 g). The yield was 37%. Itwas confirmed by mass spectrum analysis that the compound 4 wasobtained. The compound 4 had a molecular weight of 828.44 (m/e=828).

Example 5: Synthesis of Compound 5

A compound 5 was synthesized according to the following scheme.

A mixture of 1,6-dibromo-3,8-diisopropylpyrene (14 g),N,N-bis(2-methyl-5-phenylphenyl)amine (24.2 g) obtained by the step(2-3), palladium(II) acetate (0.28 g), tri-t-butylphosphine (0.51 g), atoluene solution (1 M, 75.6 mL) of LiHMDS, and xylene (280 mL) wasstirred at 110° C. for 13 hours in an argon atmosphere. The resultingreaction mixture was cooled to room temperature. After the addition ofmethanol, the resulting mixture was stirred for 0.5 hours. A solid thatprecipitated was filtered off, and purified by silica gel columnchromatography and recrystallization to obtain a compound 5 (16.6 g).The yield was 53%. It was confirmed by mass spectrum analysis that thecompound 5 was obtained. The compound 5 had a molecular weight of 980.51(m/e=980).

Example 6: Synthesis of Compound 6

A compound 6 was synthesized according to the following scheme.

(6-1) Synthesis of 3-iodo-4-methylbiphenyl

Concentrated hydrochloric acid (169 mL) was added dropwise to2-methyl-N-(o-tolyl)-5-phenylaniline (62.6 g), acetonitrile (130 mL),and ice water (200 g) at 0° C. or less, and the mixture was stirred for30 minutes. An aqueous solution (250 mL) of sodium nitrite (28.4 g) wasadded dropwise to the resulting reaction mixture at −5° C., and theresulting mixture was stirred at −5° C. for 1 hour. After the additionof an aqueous solution (200 mL) of potassium iodide (142 g) to theresulting reaction mixture at −2° C., the resulting mixture was stirredat room temperature overnight. After the addition of chloroform and asodium thiosulfate aqueous solution to the resulting reaction mixture,the resulting mixture was stirred. After separating the resultingreaction mixture, the chloroform layer was washed with water, and thesolvent was evaporated under reduced pressure. The residue was purifiedby silica gel column chromatography to obtain 3-iodo-4-methylbiphenyl(73.4 g). The yield was 73%.

(6-2) Synthesis of 2-methyl-5-phenyl-N-(3-biphenyl)aniline

A mixture of 3-iodo-4-methylbiphenyl (38 g) synthesized by the step(6-1), 3-aminobiphenyl (43.7 g),tris(dibenzylideneacetone)dipalladium(0) (4.57 g),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (2.41 g), sodiumt-butoxide (27.3 g), and xylene (820 mL) was stirred at 105° C. for 9hours in an argon atmosphere. The resulting reaction mixture was cooledto room temperature, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel column chromatographyto obtain 2-methyl-5-phenyl-N-(3-biphenyl)aniline (23 g). The yield was53%.

(6-3) Synthesis of Compound 6

A mixture of 1,6-dibromopyrene (10 g),2-methyl-5-phenyl-N-(3-biphenyl)aniline (20.5 g) obtained by the step(6-2), palladium(II) acetate (0.25 g), tri-t-butylphosphine (0.45 g), atoluene solution (1 M, 67 mL) of LiHMDS, and xylene (300 mL) was stirredat 120° C. for 18 hours in an argon atmosphere. The resulting reactionmixture was cooled to room temperature, concentrated, and purified bysilica gel column chromatography and recrystallization to obtain acompound 6 (17.9 g). The yield was 74%. It was confirmed by massspectrum analysis that the compound 6 was obtained. The compound 6 had amolecular weight of 868.38 (m/e=868).

Example 7: Synthesis of Compound 7

A compound 7 was synthesized according to the following scheme.

(7-1) Synthesis of 3-(2-methyl-5-phenylanilino)benzonitrile

A mixture of 3-aminobenzonitrile (2.41 g), 3-iodo-4-methylbiphenyl (5.0g), tris(dibenzylideneacetone)dipalladium(0) (0.23 g),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (0.32 g), sodiumt-butoxide (2.45 g), and xylene (57 mL) was stirred at 110° C. for 1hour, and then stirred at 130° C. for 2 hours in an argon atmosphere.After the addition of tris(dibenzylideneacetone)dipalladium(0) (0.23 g)and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (0.32 g), theresulting mixture was stirred for 14 hours. The resulting reactionmixture was cooled to room temperature, and the solvent was evaporatedunder reduced pressure. The residue was purified by silica gel columnchromatography to obtain 3-(2-methyl-5-phenylanilino)benzonitrile (2.32g). The yield was 48%.

(7-2) Synthesis of Compound 7

A mixture of 1,6-dibromo-3,8-diisopropylpyrene (1.65 g),3-(2-methyl-5-phenylanilino)benzonitrile (2.32 g) obtained by the step(7-1), palladium(II) acetate (0.033 g), tri-t-butylphosphinetetrafluoroborate (0.086 g), a toluene solution (1 M, 8.9 mL) of LiHMDS,and xylene (74 mL) was stirred at 120° C. overnight in an argonatmosphere. The resulting reaction mixture was cooled to roomtemperature, concentrated, and purified by silica gel columnchromatography and recrystallization to obtain a compound 7 (1.9 g). Theyield was 60%. It was confirmed by mass spectrum analysis that thecompound 7 was obtained. The compound 7 had a molecular weight of 850.40(m/e=850).

Example 8: Synthesis of Compound 8

A compound 8 was synthesized according to the following scheme.

(8-1) Synthesis of 4-methyl-3-(2-methyl-5-phenylanilino)benzonitrile

A mixture of 3-bromo-4-methylbenzonitrile (5.88 g),2-methyl-N-(o-tolyl)-5-phenylaniline (5.0 g),tris(dibenzylideneacetone)dipalladium(0) (0.50 g),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (0.68 g), sodiumt-butoxide (3.93 g), and xylene (91 mL) was stirred at 110° C. for 3.5hours in an argon atmosphere. The resulting reaction mixture was cooledto room temperature, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel column chromatographyto obtain 4-methyl-3-(2-methyl-5-phenylanilino)benzonitrile (5.25 g).The yield was 63%.

(8-2) Synthesis of Compound 8

A mixture of 1,6-dibromo-3,8-diisopropylpyrene (5.0 g),4-methyl-3-(2-methyl-5-phenylanilino)benzonitrile (7.39 g) obtained bythe step (8-1), palladium(II) acetate (0.10 g), tri-t-butylphosphinetetrafluoroborate (0.26 g), a toluene solution (1 M, 27 mL) of LiHMDS,and xylene (225 mL) was stirred at 125° C. for 6 hours in an argonatmosphere. The resulting reaction mixture was cooled to roomtemperature, and purified by silica gel column chromatography andrecrystallization to obtain a compound 8 (4.26 g). The yield was 43%. Itwas confirmed by mass spectrum analysis that the compound 8 wasobtained. The compound 8 had a molecular weight of 878.43 (m/e=878).

Example 9: Synthesis of Compound 9

A compound 9 was synthesized according to the following scheme.

(9-1) Synthesis of 4-fluoro-2-phenylbenzonitrile

A mixture of 2-bromo-4-fluorobenzonitrile (25.0 g), phenylboronic acid(18.32 g), tetrakis(triphenylphosphine)palladium (0) (2.89 g), a 2 Msodium carbonate aqueous solution (125 mL), and 1,2-dimethoxyethane(DME) (250 mL) was stirred at 80° C. for 3 hours in an argon atmosphere.The resulting reaction mixture was cooled to room temperature, andextracted with ethyl acetate. The organic layer was washed with waterand a saturated sodium chloride solution, and dried over anhydrousmagnesium sulfate, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel column chromatographyto obtain 4-fluoro-2-phenylbenzonitrile (22.1 g). The yield was 90%.

(9-2) Synthesis of 4-(2-methyl-5-phenylanilino)-2-phenylbenzonitrile

Sodium hydride (2.2 g) was added to a DMSO (32 mL) solution of2-methyl-N-(o-tolyl)-5-phenylaniline (9.16 g), and the mixture wasstirred at room temperature for 1 hour. A DMSO (31 mL) solution of4-fluoro-2-phenylbenzonitrile (4.93 g) synthesized in the step (9-1) wasadded dropwise to the resulting reaction mixture over 1 hour with watercooling, and the mixture was stirred for 6 hours. The resulting reactionmixture was diluted with toluene (150 mL). The dilution was added to ahydrochloric acid-ice mixture (100 mL), and the resulting mixture wasstirred for 1 hour. After separating the resulting mixture, the toluenelayer was washed with hydrochloric acid and a saturated sodium chloridesolution, and dried over anhydrous magnesium sulfate, and the solventwas evaporated under reduced pressure. The residue was purified bysilica gel column chromatography to obtain4-(2-methyl-5-phenylanilino)-2-phenylbenzonitrile (2.73 g). The yieldwas 30%.

(9-3) Synthesis of Compound 9

A mixture of 1,6-dibromo-3,8-diisopropylpyrene (3.5 g),4-(2-methyl-5-phenylanilino)-2-phenylbenzonitrile (5.68 g) obtained bythe step (9-2), palladium(II) acetate (0.07 g), tri-t-butylphosphinetetrafluoroborate (0.18 g), a toluene solution (1 M, 18.9 mL) of LiHMDS,and xylene (158 mL) was stirred at 125° C. for 6 hours in an argonatmosphere. The resulting reaction mixture was cooled to roomtemperature. After the addition of water, the mixture was stirred, and asolid produced was filtered off. The solid was purified by silica gelcolumn chromatography and recrystallization to obtain a compound 9 (4.8g). The yield was 60%. It was confirmed by mass spectrum analysis thatthe compound 9 was obtained. The compound 9 had a molecular weight of1,002.47 (m/e=1,002).

Example 10

Fabrication of Organic EL Device

A glass substrate provided with an ITO transparent electrode (anode) (25mm×75 mm×1.1 mm (thickness)) (manufactured by Geomatics) was subjectedto ultrasonic cleaning for 5 minutes in isopropyl alcohol, and subjectedto UV ozone cleaning for 30 minutes.

The glass substrate was then mounted on the substrate holder of a vacuumdeposition device, and a compound HI-1 was deposited on the side of theglass substrate on which the linear transparent electrode was formed soas to cover the transparent electrode to form an HI-1 film having athickness of 10 nm. The HI-1 film functions as a hole-injecting layer.

A compound HT-1 was deposited on the HI-1 film to form an HT-1 filmhaving a thickness of 80 nm on the HI-1 film. The HT-1 film functions asa first hole-transporting layer.

A compound HT-2 was deposited on the HT-1 film to form an HT-2 filmhaving a thickness of nm on the HT-1 film. The HT-2 film functions as asecond hole-transporting layer.

A compound BH-1 (host material) and the compound 1 (dopant material)were codeposited on the HT-2 film so that the ratio (weight ratio) ofthe compound 1 was 4% to form an emitting layer having a thickness of 25nm.

A compound ET-1 was deposited on the emitting layer to form anelectron-transporting layer having a thickness of 25 nm. A compound ET-2(electron-injecting material) was deposited on the electron-transportinglayer to form an electron-injecting layer having a thickness of 10 nm.LiF was deposited on the electron-injecting layer to form an LiF filmhaving a thickness of 1 nm. Al was deposited on the LiF film to form ametal cathode having a thickness of 80 nm.

An organic EL device was thus fabricated. The compounds used tofabricate the organic EL device are shown below.

Evaluation of Organic EL Device

The organic EL device was evaluated as described below. Specifically, avoltage was applied to the organic EL device so that the current densitywas 10 mA/cm², and the EL emission spectrum was measured using aspectroradiometer (“CS-1000” manufactured by Konica Minolta, Inc.). Theexternal quantum efficiency (EQE) (%) and the emission peak wavelengthwere calculated from the resulting spectral radiance spectrum. Theresults are shown in Table 1.

Examples 11 to 17 and Comparative Examples 1 to 6

An organic EL device was fabricated and evaluated in the same manner asin Example 10, except that the compound listed in Table 1 was usedinstead of the compound 1. The results are shown in Table 1.

TABLE 1 Dopant EQE Emission peak material (%) wavelength (nm) Example 10Compound 1 10.1 458 Example 11 Compound 2 10.5 459 Example 12 Compound 310.0 459 Example 13 Compound 4 10.2 461 Example 14 Compound 5 10.5 461Example 15 Compound 6 10.2 461 Example 16 Compound 7 10.1 458 Example 17Compound 8 10.0 454 Comparative Comparative 9.4 469 Example 1 compound 1Comparative Comparative 9.3 457 Example 2 compound 2 ComparativeComparative 9.6 458 Example 3 compound 3 Comparative Comparative 9.4 467Example 4 compound 4 Comparative Comparative 9.2 466 Example 5 compound5 Comparative Comparative 9.3 471 Example 6 compound 6

Example 18

Fabrication of Organic EL Device

A glass substrate provided with an ITO transparent electrode (anode) (25mm×75 mm×1.1 mm (thickness)) (manufactured by Geomatics) was subjectedto ultrasonic cleaning for 5 minutes in isopropyl alcohol, and subjectedto UV ozone cleaning for 30 minutes.

The glass substrate was then mounted on the substrate holder of a vacuumdeposition device, and a compound HI-1 was deposited on the side of theglass substrate on which the linear transparent electrode was formed soas to cover the transparent electrode to form an HI-1 film having athickness of 5 nm. The HI-1 film functions as a hole-injecting layer.

A compound HT-1 was deposited on the HI-1 film to form an HT-1 filmhaving a thickness of 90 nm on the HI-1 film. The HT-1 film functions asa first hole-transporting layer.

A compound HT-2 was deposited on the HT-1 film to form an HT-2 filmhaving a thickness of nm on the HT-1 film. The HT-2 film functions as asecond hole-transporting layer.

A compound BH-2 (host material) and the compound 1 (dopant material)were co-deposited on the HT-2 film so that the ratio (weight ratio) ofthe compound 1 was 4% to form an emitting layer having a thickness of 25nm.

A compound ET-3 was deposited on the emitting layer to form anelectron-transporting layer having a thickness of 5 nm. A compound ET-2and a compound ET-4 were deposited on the electron-transporting layer ina weight ratio of 1:1 to form an electron-injecting layer having athickness of 25 nm. A compound ET-4 was deposited on theelectron-injecting layer to form an ET-4 film having a thickness of 1nm. Al metal was deposited on the ET-4 film to form a metal cathodehaving a thickness of 80 nm.

An organic EL device was thus fabricated. The compounds used tofabricate the organic EL device are shown below.

Evaluation of Organic EL Device

The organic EL device was evaluated as described below. Specifically, avoltage was applied to the organic EL device so that the current densitywas 10 mA/cm², and the EL emission spectrum was measured using aspectroradiometer (“CS-1000” manufactured by Konica Minolta, Inc.). Theexternal quantum efficiency (EQE) (%) and the emission peak wavelengthwere calculated from the resulting spectral radiance spectrum. Theresults are shown in Table 2.

Examples 19 to 27 and Comparative Examples 7 and 8

An organic EL device was fabricated and evaluated in the same manner asin Example 18, except that the compounds listed in Table 2 were usedinstead of compound 1 and compound BH-2. The compound used to fabricatethe organic EL device is shown below. The results are shown in Table 2.

TABLE 2 Host EQE Emission peak Dopant material material (%) wavelength(nm) Example 18 Compound 1 BH-2 10.0 459 Example 19 Compound 2 BH-2 10.4459 Example 20 Compound 4 BH-2 9.9 461 Example 21 Compound 5 BH-2 10.5462 Example 22 Compound 6 BH-2 10.1 463 Example 23 Compound 1 BH-3 9.9459 Example 24 Compound 2 BH-3 10.2 459 Example 25 Compound 4 BH-3 10.0461 Example 26 Compound 5 BH-3 10.4 461 Example 27 Compound 6 BH-3 10.0462 Comparative Comparative BH-2 9.4 469 Example 7 compound 1Comparative Comparative BH-3 9.2 469 Example 8 compound 1

As is clear from Tables 1 and 2, the organic EL device fabricated usingthe compound according to one aspect of the invention exhibitedexcellent efficiency.

The compound according to one aspect of the invention achieves highefficiency due to the presence of an alkyl group situated at the orthoposition and one or more aryl groups that are bonded to at least one ofthe side-chain substituents (phenyl groups) of the diaminopyrenestructure. It is considered that energy loss when the energy obtainedfrom the host material is converted into light can be reduced when analkyl group is situated at the ortho position of the phenyl group. It isconsidered that interaction with the host material included in theemitting layer is optimized, and smooth energy transfer and emissionoccur due to one or more aryl groups, so that the luminous efficiency isimproved.

It is clear from a comparison with the comparative compounds 1, 4, and 6that the presence of an alkyl group situated at the ortho positioncontributes to an improvement in luminous efficiency. It is clear from acomparison with the comparative compounds 3 and 5 that the presence ofan aryl group contributes to an emission effect. It is considered thatthe compound according to one aspect of the invention reducesinactivation due to vibrations of the side-chain substituent as comparedwith the comparative compound 2 in which a fused-ring substituent ispresent (bonded directly) in addition to the center pyrene ring. It isconsidered that higher efficiency was thus obtained.

Although only some exemplary embodiments and/or examples of theinvention have been described in detail above, those skilled in the artwill readily appreciate that many modifications are possible in theexemplary embodiments and/or examples without materially departing fromthe novel teachings and advantages of the invention. Accordingly, allsuch modifications are intended to be included within the scope of theinvention.

The specification of the Japanese patent application to which thepresent application claims priority under the Paris Convention isincorporated herein by reference in its entirety.

The invention claimed is:
 1. An organic electroluminescence devicecomprising a cathode, an anode, and one or more organic thin film layersthat are provided between the cathode and the anode, the one or moreorganic thin film layers comprising at least an emitting layer, and atleast one organic thin film layer included in the one or more organicthin film layers comprising a compound of a formula (1) and a compoundof a formula (100),

wherein Ar is a substituted or unsubstituted phenyl group, a substitutedor unsubstituted naphthyl group, a substituted or unsubstituted anthrylgroup, a substituted or unsubstituted phenanthryl group, a substitutedor unsubstituted naphthacenyl group, a substituted or unsubstitutedpyrenyl group, a substituted or unsubstituted chrysenyl group, asubstituted or unsubstituted benzo[c]phenanthryl group, a substituted orunsubstituted benzo[g]chrysenyl group, a substituted or unsubstitutedtriphenylenyl group, a substituted or unsubstituted benzofluorenylgroup, a substituted or unsubstituted dibenzofluorenyl group, asubstituted or unsubstituted biphenylyl group, a substituted orunsubstituted o-terphenyl group, a substituted or unsubstitutedm-terphenyl group, a substituted or unsubstituted p-terphenyl group, asubstituted or unsubstituted fluoranthenyl group, R^(a) areindependently a substituted or unsubstituted alkyl group including 1 to15 carbon atoms, or a substituted or unsubstituted cycloalkyl groupincluding 3 to 15 carbon atoms, R^(b1) to R^(b4) are independently ahalogen atom, a cyano group, a substituted or unsubstituted alkyl groupincluding 1 to 15 carbon atoms, a substituted or unsubstitutedcycloalkyl group including 3 to 15 carbon atoms, a substituted orunsubstituted alkylsilyl group including 1 to 45 carbon atoms, asubstituted or unsubstituted arylsilyl group including 6 to 50 carbonatoms, a substituted or unsubstituted alkoxy group including 1 to 15carbon atoms, a substituted or unsubstituted aryloxy group including 6to 30 ring carbon atoms, a substituted or unsubstituted alkylthio groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted arylthiogroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms, R^(c1) to R^(c10) are independently a hydrogen atom, ahalogen atom, a cyano group, a substituted or unsubstituted alkyl groupincluding 1 to 15 carbon atoms, a substituted or unsubstitutedcycloalkyl group including 3 to 15 carbon atoms, a substituted orunsubstituted alkylsilyl group including 1 to 45 carbon atoms, asubstituted or unsubstituted arylsilyl group including 6 to 50 carbonatoms, a substituted or unsubstituted alkoxy group including 1 to 15carbon atoms, a substituted or unsubstituted aryloxy group including 6to 30 ring carbon atoms, a substituted or unsubstituted alkylthio groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted arylthiogroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, a substituted or unsubstituted heteroaryl group including 3 to 30ring atoms, or a single bond that is bonded to either nitrogen atom, isa bonding position at which any of R^(c1) to R^(c10) is bonded to eithernitrogen atom, x is an integer from 0 to 3, y is an integer from 0 to 4,z are independently an integer from 0 to 5, a plurality of R^(b1) areeither identical or different when x is an integer equal to or largerthan 2, a plurality of R^(b2) are either identical or different when yis an integer equal to or larger than 2, and a plurality of R^(b3) orR^(b4) are either identical or different when z is an integer equal toor larger than 2, when R^(a) is substituted with a substituent, thesubstituent is an alkyl group including 1 to 10 carbon atoms, acycloalkyl group including 3 to 10 ring carbon atoms, an alkylsilylgroup including 3 to 30 carbon atoms, an arylsilyl group including 6 to60 carbon atoms, an alkoxy group including 1 to 10 carbon atoms, aryloxygroup including 6 to 20 ring carbon atoms, an alkylthio group including1 to 10 carbon atoms, an arylthio group including 6 to 20 ring carbonatoms, an arylamino group including 12 to 30 ring carbon atoms, an arylgroup including 6 to 20 ring carbon atoms, or a heteroaryl groupincluding 5 to 20 ring atoms,

wherein Ar¹¹ and Ar¹² are independently a substituted or unsubstitutedmonocyclic group including 5 to 50 ring atoms, a substituted orunsubstituted fused ring group including 8 to 50 ring atoms, or a groupformed by a combination of the monocyclic group and the fused ringgroup, and R¹⁰¹ to R¹⁰⁸ are independently an atom or a group selectedfrom a group consisting of a hydrogen atom, a substituted orunsubstituted monocyclic group including 5 to 50 ring atoms, asubstituted or unsubstituted fused ring group including 8 to 50 ringatoms, a group formed by a combination of the monocyclic group and thefused ring group, a substituted or unsubstituted alkyl group including 1to 50 carbon atoms, a substituted or unsubstituted cycloalkyl groupincluding 3 to 50 ring carbon atoms, a substituted or unsubstitutedalkoxy group including 1 to 50 carbon atoms, a substituted orunsubstituted aralkyl group including 7 to 50 carbon atoms, asubstituted or unsubstituted aryloxy group including 6 to 50 ring carbonatoms, a substituted or unsubstituted silyl group, a halogen atom, and acyano group.
 2. The organic electroluminescence device according toclaim 1, the compound of the formula (1) being of a formula (2),

wherein Ar, R^(a), R^(b1) to R^(b4), R^(c1) to R^(c10), x, z, and * arethe same as defined for the formula (1).
 3. The organicelectroluminescence device according to claim 1, wherein R^(c1) toR^(c10) are independently a hydrogen atom, a halogen atom, a cyanogroup, a substituted or unsubstituted alkyl group including 1 to 15carbon atoms, a substituted or unsubstituted cycloalkyl group including3 to 15 carbon atoms, a substituted or unsubstituted alkylsilyl groupincluding 1 to 45 carbon atoms, a substituted or unsubstituted arylsilylgroup including 6 to 50 carbon atoms, a substituted or unsubstitutedalkoxy group including 1 to 15 carbon atoms, a substituted orunsubstituted aryloxy group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted alkylthio group including 1 to 15 carbonatoms, a substituted or unsubstituted arylthio group including 6 to 30ring carbon atoms, a substituted or unsubstituted aryl group including 6to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl groupincluding 3 to 30 ring atoms, or a single bond that is bonded to eithernitrogen atom.
 4. The organic electroluminescence device according toclaim 1, the compound of the formula (1) being of a formula (3),

wherein Ar, R^(a), R^(b1) to R^(b4), R^(c2) to R^(c10), x, z, and * arethe same as defined for the formula (1).
 5. The organicelectroluminescence device according claim 1, the compound of theformula (1) being of a formula (4),

wherein Ar, R^(a), R^(b1) to R^(b4), x, and z are the same as definedfor the formula (1), and R^(c2) to R^(c5) and R^(c7) to R^(c10) areindependently a hydrogen atom, a halogen atom, a cyano group, asubstituted or unsubstituted alkyl group including 1 to 15 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 15 carbonatoms, a substituted or unsubstituted alkylsilyl group including 1 to 45carbon atoms, a substituted or unsubstituted arylsilyl group including 6to 50 carbon atoms, a substituted or unsubstituted alkoxy groupincluding 1 to 15 carbon atoms, a substituted or unsubstituted aryloxygroup including 6 to 30 ring carbon atoms, a substituted orunsubstituted alkylthio group including 1 to 15 carbon atoms, asubstituted or unsubstituted arylthio group including 6 to 30 ringcarbon atoms, a substituted or unsubstituted arylamino group including 6to 30 ring carbon atoms, a substituted or unsubstituted aryl groupincluding 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group including 3 to 30 ring atoms.
 6. The organicelectroluminescence device according to claim 5, the compound of theformula (4) being of a formula (4-1),

wherein Ar, R^(a), R^(b1) to R^(b4), R^(c3), R^(c8), x, and z are thesame as defined for the formula (4).
 7. The organic electroluminescencedevice according to claim 6, wherein R^(c3) and R^(c8) are independentlya hydrogen atom, an alkyl group including 1 to 6 carbon atoms, or acycloalkyl group including 1 to 6 carbon atoms.
 8. The organicelectroluminescence device according to claim 5, the compound of theformula (4) being of a formula (4-1),

wherein R^(b3), R^(b4), R^(c3), R^(c8), and z are the same as definedfor the formula (4), the benzene ring-containing group to which R^(b1)is bonded is represented by a formula (10), and the benzenering-containing group to which R^(b2) is bonded is represented by aformula (11),

wherein Ar, R^(a), R^(b1), R^(b2), and x are the same as defined for theformula (1).
 9. The organic electroluminescence device according toclaim 5, the compound of the formula (4) being of a formula (4-1),

wherein R^(c3) and R^(c8) are the same as defined for the formula (4),the benzene ring-containing group to which R^(b1) is bonded isrepresented by a formula (10), the benzene ring-containing group towhich R^(b2) is bonded is represented by a formula (11), the benzenering-containing group to which R^(b3) is bonded is represented by aformula (12), and the benzene ring-containing group to which R^(b4) isbonded is represented by a formula (13),

wherein Ar, R^(a), R^(b1), R^(b2), and x are the same as defined for theformula (1),

wherein R^(b3) and R^(b4) are the same as defined for the formula (1),R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 10. The organicelectroluminescence device according to claim 5, the compound of theformula (4) being of a formula (4-1),

wherein R^(c3) and R^(c8) are the same as defined for the formula (4),the benzene ring-containing group to which R^(b1) is bonded isrepresented by a formula (10), the benzene ring-containing group towhich R^(b2) is bonded is represented by a formula (11), the benzenering-containing group to which R^(b3) is bonded is represented by aformula (12), and the benzene ring-containing group to which R^(b4) isbonded is represented by a formula (13),

wherein Ar, R^(b1), R^(b2), and x are the same as defined for theformula (1), and R^(a) are independently an unsubstituted alkyl groupincluding 1 to 6 carbon atoms,

wherein R^(b3) and R^(b4) are the same as defined for the formula (1),R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 11. The organicelectroluminescence device according to claim 5, the compound of theformula (4) being of a formula (4-1),

wherein R^(c3) and R^(c8) are the same as defined for the formula (4),the benzene ring-containing group to which R^(b1) is bonded isrepresented by a formula (10), the benzene ring-containing group towhich R^(b2) is bonded is represented by a formula (11), the benzenering-containing group to which R^(b3) is bonded is represented by aformula (12), and the benzene ring-containing group to which R^(b4) isbonded is represented by a formula (13),

wherein Ar, and x are the same as defined for the formula (1), R^(a) areindependently an unsubstituted alkyl group including 1 to 6 carbonatoms, R^(b1) and R^(b2) are independently an unsubstituted phenylgroup, or an unsubstituted alkyl group including 1 to 15 carbon atoms,

wherein R^(b3) and R^(b4) are independently an unsubstituted phenylgroup, or an unsubstituted alkyl group including 1 to 15 carbon atoms,R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 12. The organicelectroluminescence device according to claim 5, the compound of theformula (4) being of a formula (4-1),

wherein R^(c3) and R^(c8) are independently a hydrogen atom, the benzenering-containing group to which R^(b1) is bonded is represented by aformula (10), the benzene ring-containing group to which R^(b2) isbonded is represented by a formula (11), the benzene ring-containinggroup to which R^(b3) is bonded is represented by a formula (12), andthe benzene ring-containing group to which R^(b4) is bonded isrepresented by a formula (13),

wherein Ar and x are the same as defined for the formula (1), R^(a) areindependently an unsubstituted alkyl group including 1 to 6 carbonatoms, R^(b1) and R^(b2) are independently an unsubstituted phenylgroup, or an unsubstituted alkyl group including 1 to 15 carbon atoms,

wherein R^(b3) and R^(b4) are independently an unsubstituted phenylgroup, or an unsubstituted alkyl group including 1 to 15 carbon atoms,R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 13. The organicelectroluminescence device according to claim 5, the compound of theformula (4) being of a formula (4-1),

wherein R^(c3) and R^(c8) are independently a hydrogen atom, the benzenering-containing group to which R^(b1) is bonded is represented by aformula (10), the benzene ring-containing group to which R^(b2) isbonded is represented by a formula (11), the benzene ring-containinggroup to which R^(b3) is bonded is represented by a formula (12), andthe benzene ring-containing group to which R^(b4) is bonded isrepresented by a formula (13),

wherein Ar are the same as defined for the formula (1), R^(a) areindependently an unsubstituted alkyl group including 1 to 6 carbonatoms, R^(b1) and R^(b2) are independently an unsubstituted phenylgroup, or an unsubstituted alkyl group including 1 to 15 carbon atoms,and x are 0,

wherein R^(b3) and R^(b4) are independently an unsubstituted phenylgroup, or an unsubstituted alkyl group including 1 to 15 carbon atoms,R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are
 1. 14. The organic electroluminescence device according to claim 1,the compound of the formula (1) being of a formula (5),

wherein Ar, R^(a), R^(b1) to R^(b4), x, and z are the same as definedfor the formula (1), and R^(c2) and R^(c4) to R^(c10) are independentlya hydrogen atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, a substituted or unsubstituted alkoxy group including 1 to15 carbon atoms, a substituted or unsubstituted aryloxy group including6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 15 carbon atoms, a substituted or unsubstitutedarylthio group including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms.
 15. The organic electroluminescence device to claim 14,the compound of the formula (5) being of a formula (5-1),

wherein Ar, R^(a), R^(b1) to R^(b4), x, and z are the same as definedfor the formula (5).
 16. The organic electroluminescence deviceaccording to claim 15, wherein R^(c7) is a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms.
 17. Theorganic electroluminescence device according to claim 1, wherein thebenzene ring-containing group to which R^(b1) is bonded has a structurein which R^(b1) and Ar are not bonded at the para position with respectto the bonding position at which the N atom is bonded, and the benzenering-containing group to which R^(b2) is bonded has a structure in whichR^(b2) is not bonded at the para position with respect to the bondingposition at which the N atom is bonded.
 18. The organicelectroluminescence device according to claim 1, wherein the benzenering-containing group to which R^(b1) is bonded is represented by aformula (10), and the benzene ring-containing group to which R^(b2) isbonded is represented by a formula (11),

wherein Ar, R^(a), R^(b1), R^(b2), and x are the same as defined for theformula (1).
 19. The organic electroluminescence device according toclaim 1, wherein the benzene ring-containing group to which R^(b3) isbonded is represented by a formula (12), and the benzene ring-containinggroup to which R^(b4) is bonded is represented by a formula (13),

wherein R^(b3) and R^(b4) are the same as defined for the formula (1),R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 20. The organicelectroluminescence device according to claim 1, wherein R^(b1) toR^(b4) in the formula (1) are independently a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, a substituted or unsubstituted alkoxy group including 1 to15 carbon atoms, a substituted or unsubstituted aryloxy group including6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 15 carbon atoms, a substituted or unsubstitutedarylthio group including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms.
 21. The organic electroluminescence device according toclaim 1, wherein R^(b1) to R^(b4) in the formula (1) are independently acyano group, an unsubstituted phenyl group, a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, or a substituted or unsubstituted aryl group including 6to 30 ring carbon atoms.
 22. The organic electroluminescence deviceaccording to claim 1, wherein R^(b1) to R^(b4) in the formula (1) areindependently an unsubstituted phenyl group, or an unsubstituted alkylgroup including 1 to 15 carbon atoms.
 23. The organicelectroluminescence device according to claim 1, wherein R^(a) in theformula (1) are independently a substituted or unsubstituted alkyl groupincluding 1 to 6 carbon atoms.
 24. The organic electroluminescencedevice according to claim 1, wherein R^(a) in the formula (1) areindependently an unsubstituted alkyl group including 1 to 15 carbonatoms, or an unsubstituted cycloalkyl group including 3 to 15 carbonatoms.
 25. The organic electroluminescence device according to claim 1,the compound of the formula (1) being an emitting material.
 26. Theorganic electroluminescence device according to claim 1, the compound ofthe formula (1) being a doping material.
 27. The organicelectroluminescence device according to claim 1, wherein the at leastone organic thin film layer is the emitting layer.
 28. The organicelectroluminescence device according to claim 1, wherein Ar¹¹ and Ar¹²in the formula (100) are independently a substituted or unsubstitutedfused ring group including 8 to 50 ring carbon atoms.
 29. The organicelectroluminescence device according to claim 28, wherein Ar¹² in theformula (100) is a substituted or unsubstituted fused ring groupincluding 8 to 50 ring atoms, and Ar¹¹ in the formula (100) is anunsubstituted naphthyl group.
 30. The organic electroluminescence deviceaccording to claim 1, wherein one of Ar¹¹ and Ar¹² in the formula (100)is a substituted or unsubstituted monocyclic group including 5 to 50ring atoms, and the other of Ar¹¹ and Ar¹² in the formula (100) is asubstituted or unsubstituted fused ring group including 8 to 50 ringatoms.
 31. The organic electroluminescence device according to claim 30,wherein Ar¹² in the formula (100) is a naphthyl group, a phenanthrylgroup, a benzanthryl group, a fluorenyl group, or a dibenzofuranylgroup, and Ar¹¹ in the formula (100) is an unsubstituted phenyl group,or a phenyl group substituted with a monocyclic group or a fused ringgroup.
 32. The organic electroluminescence device according to claim 30,wherein Ar¹² in the formula (100) is a substituted or unsubstituteddibenzofuranyl group or a substituted or unsubstitutednaphthodibenzofuranyl group, and Ar¹¹ in the formula (100) is anunsubstituted phenyl group, or a phenyl group substituted with amonocyclic group or a fused ring group.
 33. The organicelectroluminescence device according to claim 30, wherein Ar¹² in theformula (100) is a substituted or unsubstituted fused ring groupincluding 8 to 50 ring atoms, and Ar¹¹ in the formula (100) is anunsubstituted phenyl group.
 34. The organic electroluminescence deviceaccording to claim 1, wherein Ar¹¹ and Ar¹² in the formula (100) areindependently a substituted or unsubstituted monocyclic group including5 to 50 ring atoms.
 35. The organic electroluminescence device accordingto claim 34, wherein Ar¹¹ and Ar¹² in the formula (100) areindependently a substituted or unsubstituted phenyl group.
 36. Theorganic electroluminescence device according to claim 35, wherein Ar¹¹in the formula (100) is an unsubstituted phenyl group, and Ar¹² in theformula (100) is a phenyl group substituted with a monocyclic group or afused ring group.
 37. The organic electroluminescence device accordingto claim 35, wherein Ar¹¹ and Ar¹² in the formula (100) areindependently a phenyl group substituted with a monocyclic group or afused ring group.
 38. An electronic apparatus comprising the organicelectroluminescence device according to claim
 1. 39. The organicelectroluminescence device according claim 1, the compound of theformula (1) being of a formula (4),

wherein z, R^(b3) and R^(b4) are the same as defined for the formula(1), and R^(c2) to R^(c5) and R^(c7) to R^(c10) are independently ahydrogen atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, a substituted or unsubstituted alkoxy group including 1 to15 carbon atoms, a substituted or unsubstituted aryloxy group including6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 15 carbon atoms, a substituted or unsubstitutedarylthio group including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms, the benzene ring-containing group to which R^(b1) isbonded is represented by a formula (10), and the benzene ring-containinggroup to which R^(b2) is bonded is represented by a formula (11),

wherein Ar, R^(a), R^(b1), R^(b2), and x are the same as defined for theformula (1).
 40. The organic electroluminescence device according claim1, the compound of the formula (1) being of a formula (4),

wherein R^(c2) to R^(c5) and R^(c7) to R^(c10) are independently ahydrogen atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, a substituted or unsubstituted alkoxy group including 1 to15 carbon atoms, a substituted or unsubstituted aryloxy group including6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 15 carbon atoms, a substituted or unsubstitutedarylthio group including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms, the benzene ring-containing group to which R^(b1) isbonded is represented by a formula (10), the benzene ring-containinggroup to which R^(b2) is bonded is represented by a formula (11), thebenzene ring-containing group to which R^(b3) is bonded is representedby a formula (12), and the benzene ring-containing group to which R^(b4)is bonded is represented by a formula (13),

wherein Ar, R^(a), R^(b1), R^(b2), and x are the same as defined for theformula (1),

wherein R^(b3) and R^(b4) are the same as defined for the formula (1),R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 41. The organicelectroluminescence device according claim 1, the compound of theformula (1) being of a formula (4),

wherein R^(c2) to R^(c5) and R^(c7) to R^(c10) are independently ahydrogen atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, a substituted or unsubstituted alkoxy group including 1 to15 carbon atoms, a substituted or unsubstituted aryloxy group including6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 15 carbon atoms, a substituted or unsubstitutedarylthio group including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms, the benzene ring-containing group to which R^(b1) isbonded is represented by a formula (10), the benzene ring-containinggroup to which R^(b2) is bonded is represented by a formula (11), thebenzene ring-containing group to which R^(b3) is bonded is representedby a formula (12), and the benzene ring-containing group to which R^(b4)is bonded is represented by a formula (13),

wherein Ar, R^(b1), R^(b2), and x are the same as defined for theformula (1), and R^(a) are independently an unsubstituted alkyl groupincluding 1 to 6 carbon atoms,

wherein R^(b3) and R^(b4) are the same as defined for the formula (1),R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 42. The organicelectroluminescence device according claim 1, the compound of theformula (1) being of a formula (4),

wherein R^(c2) to R^(c5) and R^(c7) to R^(c10) are independently ahydrogen atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group including 1 to 15 carbon atoms, a substitutedor unsubstituted cycloalkyl group including 3 to 15 carbon atoms, asubstituted or unsubstituted alkylsilyl group including 1 to 45 carbonatoms, a substituted or unsubstituted arylsilyl group including 6 to 50carbon atoms, a substituted or unsubstituted alkoxy group including 1 to15 carbon atoms, a substituted or unsubstituted aryloxy group including6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 15 carbon atoms, a substituted or unsubstitutedarylthio group including 6 to 30 ring carbon atoms, a substituted orunsubstituted arylamino group including 6 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group including 3 to30 ring atoms, the benzene ring-containing group to which R^(b1) isbonded is represented by a formula (10), the benzene ring-containinggroup to which R^(b2) is bonded is represented by a formula (11), thebenzene ring-containing group to which R^(b3) is bonded is representedby a formula (12), and the benzene ring-containing group to which R^(b4)is bonded is represented by a formula (13),

wherein Ar, and x are the same as defined for the formula (1), R^(a) areindependently an unsubstituted alkyl group including 1 to 6 carbonatoms, and R^(b1) and R^(b2) are independently an unsubstituted phenylgroup or an unsubstituted alkyl group including 1 to 15 carbon atoms,

wherein R^(b3) and R^(b4) are independently an unsubstituted phenylgroup or an unsubstituted alkyl group including 1 to 15 carbon atoms,R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 43. The organicelectroluminescence device according claim 1, the compound of theformula (1) being of a formula (4),

wherein R^(c2) to R^(c5) and R^(c7) to R^(c10) are independently ahydrogen atom, the benzene ring-containing group to which R^(b1) isbonded is represented by a formula (10), the benzene ring-containinggroup to which R^(b2) is bonded is represented by a formula (11), thebenzene ring-containing group to which R^(b3) is bonded is representedby a formula (12), and the benzene ring-containing group to which R^(b4)is bonded is represented by a formula (13),

wherein Ar, and x are the same as defined for the formula (1), R^(a) areindependently an unsubstituted alkyl group including 1 to 6 carbonatoms, and R^(b1) and R^(b2) are independently an unsubstituted phenylgroup or an unsubstituted alkyl group including 1 to 15 carbon atoms,

wherein R^(b3) and R^(b4) are independently an unsubstituted phenylgroup or an unsubstituted alkyl group including 1 to 15 carbon atoms,R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are independently an integer from 0 to
 4. 44. The organicelectroluminescence device according claim 1, the compound of theformula (1) being of a formula (4),

wherein R^(c2) to R^(c5) and R^(c7) to R^(c10) are independently ahydrogen atom, the benzene ring-containing group to which R^(b1) isbonded is represented by a formula (10), the benzene ring-containinggroup to which R^(b2) is bonded is represented by a formula (11), thebenzene ring-containing group to which R^(b3) is bonded is representedby a formula (12), and the benzene ring-containing group to which R^(b4)is bonded is represented by a formula (13),

wherein Ar are the same as defined for the formula (1), R^(a) areindependently an unsubstituted alkyl group including 1 to 6 carbonatoms, and x are 0,

wherein R^(b3) and R^(b4) are independently an unsubstituted phenylgroup or an unsubstituted alkyl group including 1 to 15 carbon atoms,R^(b3′) and R^(b4′) are independently a substituted or unsubstitutedalkyl group including 1 to 15 carbon atoms, or a substituted orunsubstituted cycloalkyl group including 3 to 15 carbon atoms, and z1are 1.